Career
Winn is a 2008 graduate of the University of Detroit Jesuit High School. He played college football at Cincinnati. He originally signed with the Houston Texans as an undrafted free agent in 2013.
Houston Texans
On April 28, 2013, Winn signed with the Houston Texans as an undrafted free agent.
New England Patriots
On June 17, 2013, he signed with the New England Patriots. Oakland Raiders
The Raiders released Winn from the practice squad on October 15, 2013.
Pittsburgh Steelers
The Steelers signed Winn to their practice squad on October 22, 2013. He was released on November 19, 2013 and replaced by Ray Graham, another undrafted free agent initially signed by the Houston Texans.
Dallas Cowboys
On December 4, 2013, Winn signed with the Dallas Cowboys practice squad.
The Cowboys waived Winn on December 17, 2013. Detroit Lions
During the 2014 offseason, Winn tried out for the Atlanta Falcons, but was not signed. Afterwards, the Detroit Lions signed him on July 16, 2014.
He played twelve games for the Lions in 2014, gaining 73 yards on 19 carries.
He was placed on the Lions" practice at the start of the 2015 season, but moved to the main club on October 19 after an injury to Zach Zenner.